Abstract
Charge-transfer complexation of m-nitrobenzoic acid (1) with aromatic hydrocarbons was found to exhibit size and shape selectivity: naphthalene or its 2,7-dimethyl and 2,3,6,7-tetramethyl derivatives failed to afford crystalline complexes with 1 whereas yellow crystals containing a stoichiometric amount of 2,3- or 2,6-dimethylnaphthalene, biphenylene, or anthracene were obtained by the direct method in CH2Cl2. X-ray analyses on these complexes have revealed dimer formation of 1 by O−H···O hydrogen bonding, yet the important structural motif observed as a common feature is the two-dimensional sheetlike network, in which the dimers of 1 are further connected by C−H···O hydrogen bonding to form a series of inclusion lattices that incorporate hydrocarbon guests. Such a supramolecular aggregation by C−H···O bonding was proven to take a significant part in the recognition properties of 1 to differentiate the dimethylnaphthalene isomers in its complexation process.
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